PL130844B1 - Herbicide and method of manufacture of novel derivatives of delta-2-upwards-1,2,4-triazolin-5-one - Google Patents
Herbicide and method of manufacture of novel derivatives of delta-2-upwards-1,2,4-triazolin-5-one Download PDFInfo
- Publication number
- PL130844B1 PL130844B1 PL1981234419A PL23441981A PL130844B1 PL 130844 B1 PL130844 B1 PL 130844B1 PL 1981234419 A PL1981234419 A PL 1981234419A PL 23441981 A PL23441981 A PL 23441981A PL 130844 B1 PL130844 B1 PL 130844B1
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- Poland
- Prior art keywords
- formula
- radical
- compound
- triazolinone
- difluoromethyl
- Prior art date
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- 230000002363 herbicidal effect Effects 0.000 title claims description 38
- 239000004009 herbicide Substances 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 21
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 C1-C4-alkyl radical Chemical group 0.000 claims description 59
- 150000001875 compounds Chemical class 0.000 claims description 39
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- 239000000126 substance Substances 0.000 claims description 23
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- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical group F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 8
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- 238000004090 dissolution Methods 0.000 description 1
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- OUYDEKFRLSFDMU-UHFFFAOYSA-N ethyl 2-(4-chloro-2-methylphenoxy)acetate Chemical compound CCOC(=O)COC1=CC=C(Cl)C=C1C OUYDEKFRLSFDMU-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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- 239000002480 mineral oil Substances 0.000 description 1
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 description 1
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- MQHNKCZKNAJROC-UHFFFAOYSA-N phthalic acid dipropyl ester Natural products CCCOC(=O)C1=CC=CC=C1C(=O)OCCC MQHNKCZKNAJROC-UHFFFAOYSA-N 0.000 description 1
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- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
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- STAPBGVGYWCRTF-UHFFFAOYSA-M sodium;2-(4-chloro-2-methylphenoxy)acetate Chemical compound [Na+].CC1=CC(Cl)=CC=C1OCC([O-])=O STAPBGVGYWCRTF-UHFFFAOYSA-M 0.000 description 1
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- 239000011593 sulfur Substances 0.000 description 1
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- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18455780A JPS57108079A (en) | 1980-12-25 | 1980-12-25 | Delta2-1,2,4-triazolin-5-one deriviative, its preparation and use |
| JP18455880A JPS57108080A (en) | 1980-12-25 | 1980-12-25 | Delta2-1,2,4-triazolin-5-ones, their preparations and uses |
| JP6549781A JPS57181069A (en) | 1981-04-30 | 1981-04-30 | Delta2-1,2,4-triazolin-5-one and its preparation and use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL234419A1 PL234419A1 (de) | 1982-08-16 |
| PL130844B1 true PL130844B1 (en) | 1984-09-29 |
Family
ID=27298813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1981234419A PL130844B1 (en) | 1980-12-25 | 1981-12-23 | Herbicide and method of manufacture of novel derivatives of delta-2-upwards-1,2,4-triazolin-5-one |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4398943A (de) |
| AR (1) | AR228884A1 (de) |
| AT (1) | AT384526B (de) |
| AU (1) | AU545957B2 (de) |
| BE (1) | BE891607A (de) |
| BR (1) | BR8108337A (de) |
| CA (1) | CA1173046A (de) |
| CH (1) | CH651029A5 (de) |
| CS (1) | CS227028B2 (de) |
| DD (1) | DD202375A5 (de) |
| DE (1) | DE3149896A1 (de) |
| DK (1) | DK574581A (de) |
| ES (1) | ES508336A0 (de) |
| FR (1) | FR2497201A1 (de) |
| GB (1) | GB2090250B (de) |
| HU (1) | HU187389B (de) |
| IL (1) | IL64615A (de) |
| IT (1) | IT1146733B (de) |
| NL (1) | NL8105748A (de) |
| PH (1) | PH17705A (de) |
| PL (1) | PL130844B1 (de) |
| PT (1) | PT74200B (de) |
| RO (1) | RO85264B (de) |
| SE (1) | SE442113B (de) |
| SU (1) | SU1309910A3 (de) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4919708A (en) * | 1983-10-13 | 1990-04-24 | Fmc Corporation | Haloalkyl triazolinones and herbicidal use thereof |
| US5136868A (en) * | 1983-11-04 | 1992-08-11 | Fmc Corporation | Herbicidal 1-aryl-4-substituted-1,4-dihydro-5h-tetrazol-5-ones and sulfur analogs thereof |
| BR8506209A (pt) * | 1984-03-29 | 1986-04-15 | Fmc Corp | 1-aril-delta2-1,2,4-triazolin-5-onas herbicidas |
| CA1242730A (en) * | 1984-05-31 | 1988-10-04 | Atsushi Tsushima | .delta..SUP.2-1,2,4-TRIAZOLIN-5-ONE DERIVATIVES AND HERBICIDAL COMPOSITIONS CONTAINING THE SAME |
| US4705557A (en) * | 1984-09-13 | 1987-11-10 | Fmc Corporation | Herbicidal 1-aryl-Δ2 -1,2,4-triazolin-5-ones and sulfur analogs thereof |
| WO1986002642A1 (en) * | 1984-10-31 | 1986-05-09 | Fmc Corporation | Herbicidal aryl triazolinones |
| US4818276A (en) * | 1984-11-20 | 1989-04-04 | Fmc Corporation | Herbicidal 1-aryl-Δ2 -1,2,4-triazolin-5-ones |
| EP0193660A1 (de) * | 1985-03-01 | 1986-09-10 | Nihon Nohyaku Co., Ltd. | 1-(Hydroxyphenyl)-3-methyl-4-difluormethyl-(delta-2)-1,2,4-triazolin-5-on-Derivate |
| AU4729685A (en) * | 1985-08-08 | 1987-03-05 | Fmc Corporation | Herbicidal 1-aryl-delta2 -1,2,4-triazolin-5-ones |
| JPS6299368A (ja) * | 1985-10-26 | 1987-05-08 | Nippon Nohyaku Co Ltd | Δ↑２−１，２，４−トリアゾリン−５−オン誘導体及びその製法並びにその用途 |
| EP0220952A1 (de) * | 1985-10-26 | 1987-05-06 | Nihon Nohyaku Co., Ltd. | Verfahren zur Herstellung von 1,2,4-Triazolin-5-on-Derivaten und Vorprodukte dafür |
| US5041155A (en) * | 1989-04-03 | 1991-08-20 | Fmc Corporation | Herbicidal aryl triazolinones |
| US5174809A (en) * | 1985-12-20 | 1992-12-29 | Fmc Corporation | Herbicidal aryl triazolinones |
| US5294595A (en) * | 1985-12-20 | 1994-03-15 | Fmc Corporation | Herbicidal aryl triazolinones |
| US5214154A (en) * | 1985-12-20 | 1993-05-25 | Fmc Corporation | Herbicidal aryl triazolinones |
| US4906284A (en) * | 1986-03-25 | 1990-03-06 | Fmc Corporation | Herbicidal fluoropropyl compounds |
| HUT48799A (en) * | 1986-08-20 | 1989-07-28 | Fmc Corp | Herbicides containing as active substance derivatives of triazolinon and process for production of the active substances |
| USH774H (en) | 1986-12-05 | 1990-05-01 | Nihon Nohyaku Co., Ltd. | R-enantiomers of a Δ2 -1,2,4-triazolin-5-one derivatives |
| WO1988009617A1 (en) * | 1987-06-12 | 1988-12-15 | Fmc Corporation | 1-(4-chloro-2-fluoro-5-methoxyphenyl)-3-methyl-4-difluoromethyl-delta2-1,2,4-triazolin-5-one as herbicidal agent |
| US4846875A (en) * | 1987-07-21 | 1989-07-11 | Fmc Corporation | Herbicidal triazolinones |
| US5217520A (en) * | 1988-08-31 | 1993-06-08 | Fmc Corporation | Herbicidal triazolinones |
| UA26918C2 (uk) | 1988-08-31 | 1999-12-29 | Фмк Корпорейшн | Похідhі триазоліhоhу, що проявляють гербіцидhу активhість, гербіцидhа композиція, спосіб придушеhhя росту бур'яhів |
| US5208212A (en) * | 1988-08-31 | 1993-05-04 | Fmc Corporation | Herbicidal compositions containing triazolinones |
| US5125958A (en) * | 1988-08-31 | 1992-06-30 | Fmc Corporation | Herbicidal triazolinones |
| US5298502A (en) * | 1988-12-12 | 1994-03-29 | Fmc Corporation | Method and composition for photodynamic treatment and detection of tumors |
| NZ231658A (en) * | 1988-12-12 | 1992-05-26 | Fmc Corp | Inhibitors of protoporphyrinogen oxidase and compositions for killing tumour cells |
| ATE171595T1 (de) * | 1993-10-22 | 1998-10-15 | Fmc Corp | Herbizide triazolinone |
| US5750130A (en) * | 1995-02-07 | 1998-05-12 | Ferrell; Paul | Presticide compositions |
| EP0784053A1 (de) * | 1996-01-15 | 1997-07-16 | Degussa Aktiengesellschaft | Verfahren zur Herstellung von Triazolinonherbiziden |
| USD899128S1 (en) * | 2019-01-30 | 2020-10-20 | Amini Innovation Corporation | Chair |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2725148A1 (de) | 1977-06-03 | 1978-12-14 | Hoechst Ag | 1-aryl-4-alkyl-1,2,4-triazol-5-one und verfahren zu ihrer herstellung |
| US4276420A (en) * | 1978-05-24 | 1981-06-30 | Chevron Research Company | Herbicidal and plant-growth-regulating 1,2,4-trisubstituted-1,2,4-triazolidin-3-one-5-thione |
| IT1096333B (it) * | 1978-05-25 | 1985-08-26 | Montedison Spa | 1,2,4-triazolidin-3-oni e-tioni |
| US4318731A (en) * | 1979-08-25 | 1982-03-09 | Nihon Nohyaku Co., Ltd. | Δ2 -1,2,4-triazolin-5-one derivatives and herbicidal usage thereof |
-
1981
- 1981-12-10 CH CH7879/81A patent/CH651029A5/de not_active IP Right Cessation
- 1981-12-14 CA CA000392220A patent/CA1173046A/en not_active Expired
- 1981-12-15 US US06/331,064 patent/US4398943A/en not_active Expired - Fee Related
- 1981-12-15 GB GB8137782A patent/GB2090250B/en not_active Expired
- 1981-12-16 DE DE19813149896 patent/DE3149896A1/de not_active Withdrawn
- 1981-12-16 RO RO106019A patent/RO85264B/ro unknown
- 1981-12-21 AT AT0549981A patent/AT384526B/de not_active IP Right Cessation
- 1981-12-21 NL NL8105748A patent/NL8105748A/nl not_active Application Discontinuation
- 1981-12-21 AR AR287878A patent/AR228884A1/es active
- 1981-12-22 IL IL64615A patent/IL64615A/xx unknown
- 1981-12-22 AU AU78768/81A patent/AU545957B2/en not_active Ceased
- 1981-12-22 BR BR8108337A patent/BR8108337A/pt unknown
- 1981-12-22 SE SE8107703A patent/SE442113B/sv not_active IP Right Cessation
- 1981-12-23 PL PL1981234419A patent/PL130844B1/pl unknown
- 1981-12-23 ES ES508336A patent/ES508336A0/es active Granted
- 1981-12-23 IT IT68679/81A patent/IT1146733B/it active
- 1981-12-23 PT PT74200A patent/PT74200B/pt unknown
- 1981-12-23 CS CS819741A patent/CS227028B2/cs unknown
- 1981-12-23 HU HU813939A patent/HU187389B/hu not_active IP Right Cessation
- 1981-12-23 BE BE0/206923A patent/BE891607A/fr not_active IP Right Cessation
- 1981-12-23 DK DK574581A patent/DK574581A/da not_active Application Discontinuation
- 1981-12-24 DD DD81236281A patent/DD202375A5/de unknown
- 1981-12-24 FR FR8124220A patent/FR2497201A1/fr active Granted
- 1981-12-28 PH PH26681A patent/PH17705A/en unknown
-
1982
- 1982-06-17 SU SU823451242A patent/SU1309910A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| RO85264A (ro) | 1984-09-29 |
| NL8105748A (nl) | 1982-07-16 |
| DK574581A (da) | 1982-06-26 |
| RO85264B (ro) | 1984-10-30 |
| GB2090250A (en) | 1982-07-07 |
| SU1309910A3 (ru) | 1987-05-07 |
| HU187389B (en) | 1985-12-28 |
| BE891607A (fr) | 1982-06-23 |
| FR2497201B1 (de) | 1985-02-22 |
| PL234419A1 (de) | 1982-08-16 |
| ATA549981A (de) | 1987-05-15 |
| BR8108337A (pt) | 1982-10-05 |
| SE442113B (sv) | 1985-12-02 |
| SE8107703L (sv) | 1982-06-26 |
| IT1146733B (it) | 1986-11-19 |
| IL64615A0 (en) | 1982-03-31 |
| ES8304102A1 (es) | 1983-02-16 |
| CA1173046A (en) | 1984-08-21 |
| IL64615A (en) | 1985-04-30 |
| IT8168679A0 (it) | 1981-12-23 |
| US4398943A (en) | 1983-08-16 |
| FR2497201A1 (fr) | 1982-07-02 |
| AR228884A1 (es) | 1983-04-29 |
| GB2090250B (en) | 1984-09-12 |
| DD202375A5 (de) | 1983-09-14 |
| AU7876881A (en) | 1982-07-01 |
| ES508336A0 (es) | 1983-02-16 |
| CS227028B2 (en) | 1984-04-16 |
| PH17705A (en) | 1984-11-19 |
| DE3149896A1 (de) | 1982-08-12 |
| PT74200B (en) | 1983-05-20 |
| AU545957B2 (en) | 1985-08-08 |
| AT384526B (de) | 1987-11-25 |
| CH651029A5 (de) | 1985-08-30 |
| PT74200A (en) | 1982-01-01 |
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